Fungicidal composition comprising a pyridylethylbenzamide derivative and a compound capable of inhibiting the ergosterol biosynthesis

ABSTRACT

A composition comprising at least a pyridylethylbenzamide derivative of general formula (I) (a) and a compound capable of inhibiting the ergosterol biosynthesis (b) in a (a)/(b) weight ratio of from 0.01 to 20. A composition further comprising an additional fungicidal compound. A method for preventively or curatively combating the phytopathogenic fungi of crops by using this composition.

The present application is a continuation of U.S. application Ser. No.15/232,677, filed Aug. 9, 2016, which is a continuation of Ser. No.13/430,477 filed on Mar. 26, 2012, which is a continuation of U.S.application Ser. No. 10/587,801 filed on Jul. 31, 2006, now U.S. Pat.No. 8,160,660 B2 issued on May 1, 2012, which is a 35 U.S.C. § 371national phase conversion of PCT/EP2005/002568 filed on Feb. 10, 2005,which claims priority of European Application No. 04356014.3 filed onFeb. 12, 2004 and U.S. Provisional Application No. 60/636,956 filed onDec. 17, 2004. Applicants claim priority to each of the foregoing patentapplications. The PCT International Application was published in theEnglish language.

The present invention relates to novel fungicide compositions comprisinga pyridylethylbenzamide derivative and a compound capable of inhibitingthe ergosterol biosynthesis. The present invention also relates to amethod of combating or controlling phytopathogenic fungi by applying ata locus infested or liable to be infested such a composition.

International patent application WO 01/11965 generically disclosesnumerous pyridylethylbenzamide derivatives. The possibility of combiningone or more of these numerous pyridylethylbenzamide derivatives withknown fungicidal products to develop a fungicidal activity is disclosedin general terms, without any specific example or biological data.

It is always of high-interest in agriculture to use novel pesticidalmixtures showing a synergistic effect in order notably to avoid or tocontrol the development of resistant strains to the active ingredientsor to the mixtures of known active ingredients used by the farmer whileminimising the doses of chemical products spread in the environment andreducing the cost of the treatment.

We have now found some novel fungicidal compositions which possess theabove mentioned characteristics.

Accordingly, the present invention relates to a composition comprising:

a) a pyridylethylbenzamide derivative of general formula (I)

in which:

p is an integer equal to 1, 2, 3 or 4;

q is an integer equal to 1, 2, 3, 4 or 5;

each substituent X is chosen, independently of the others, as beinghalogen, alkyl or haloalkyl;

each substituent Y is chosen, independently of the others, as beinghalogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, amino, phenoxy,alkylthio, dialkylamino, acyl, cyano, ester, hydroxy, aminoalkyl,benzyl, haloalkoxy, halosulphonyl, halothioalkyl, alkoxyalkenyl,alkylsulphonamide, nitro, alkylsulphonyl, phenylsulphonyl orbenzylsulphonyl;

as to the N-oxides of 2-pyridine thereof;

and

b) a compound capable of inhibiting the ergosterol biosynthesis;

in a (a)/(b) weight ratio of from 0.01 to 20.

In the context of the present invention:

halogen means chlorine, bromine, iodine or fluorine;

each of the alkyl or acyl radicals present in the molecule contains from1 to 10 carbon atoms, preferably from 1 to 7 carbon atoms, morepreferably from 1 to 5 carbon atoms, and may be linear or branched;

each of the alkenyl or alkynyl radicals present in the molecule containsfrom 2 to 10 carbon atoms, preferably from 2 to 7 carbon atoms, morepreferably from 2 to 5 carbon atoms, and may be linear or branched.

The composition according to the present invention provides asynergistic effect. This synergistic effect allows a reduction of thechemical substances spread into the environment and a reduction of thecost of the fungal treatment.

In the context of the present invention, the term “synergistic effect”is defined by Colby according to the article entitled “Calculation ofthe synergistic and antagonistic responses of herbicide combinations”Weeds, (1967), 15, pages 20-22.

The latter article mentions the formula:

$E = {x + y - \frac{x*y}{100}}$in which E represents the expected percentage of inhibition of thedisease for the combination of the two fungicides at defined doses (forexample equal to x and y respectively), x is the percentage ofinhibition observed for the disease by the compound (I) at a defineddose (equal to x), y is the percentage of inhibition observed for thedisease by the compound (II) at a defined dose (equal to y). When thepercentage of inhibition observed for the combination is greater than E,there is a synergistic effect.

The composition according to the present invention comprises apyridylethylbenzamide derivative of general formula (I). Preferably, thepresent invention relates to a composition comprising apyridylethylbenzamide derivative of general formula (I) in which thedifferent characteristics may be chosen alone or in combination asbeing:

-   -   as regards p, p is 2;    -   as regards q, q is 1 or 2. More preferably, q is 2;    -   as regards X, X is chosen, independently of the others, as being        halogen or haloalkyl. More preferably, X is chosen,        independently of the others, as being a chloro atom or a        trifluoromethyl group;    -   as regards Y, Y is chosen, independently of the others, as being        halogen or haloalkyl. More preferably, Y is chosen,        independently of the others, as being a chloro atom or a        trifluoromethyl group;

More preferably, the pyridylethylbenzamide derivative of general formula(I) present in the composition of the present invention is:

-   -   N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide        (compound 1);    -   N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-iodobenzamide        (compound 2); or    -   N-{2-[3,5-dichloro-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide        (compound 3).

Even more preferably, the pyridylethylbenzamide derivative of generalformula (I) present in the composition of the present invention isN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide(compound 1).

The composition according to the present invention comprises a compoundcapable of inhibiting the ergosterol biosynthesis. Preferably, thepresent invention relates to a composition comprising a compound capableof inhibiting the ergosterol biosynthesis selected from triazolederivatives, imidazole derivatives, morpholine derivatives, piperidinederivatives, fenhexamid, spiroxamine or triforine. Spiroxamine,triforine and fenhexamid are preferred.

Triazole derivatives are also preferred. According to the presentinvention, triazole derivatives may for example be azaconazole,bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole,epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol,hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil,penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole,tetraconazole, triadimefon, triadimenol, triticonazole, diclobutrazole,etaconazole, fluotrimazole, furconazole, furconazole-cis, triamiphos,triazbutil. Cyproconazole, fluquinconazole, prothioconazole andtebuconazole are still preferred.

Imidazole derivatives are also preferred. According to the presentinvention, imidazole derivatives may for example be imazalil,prochloraz, oxpoconazole fumarate, pefurazoate or triflumizole.Prochloraz is still preferred.

Morpholine derivatives are also preferred. According to the presentinvention, morpholine derivatives may for example be aldimorph,dodemorph, fenpropimorph or tridemorph. Fenpropimorph and tridemorph arestill preferred.

Piperidine derivatives are also preferred. According to the presentinvention, piperidine derivatives may for example be fenpropidin orpiperalin.

The composition according to the present invention comprises at least apyridylethylbenzamide derivative of general formula (I) (a) and acompound capable of inhibiting the ergosterol biosynthesis (b) in an(a)/(b) weight ratio of from 0.01 to 20; preferably of from 0.05 to 10;even more preferably, of from 0.1 to 5.

The composition of the present invention may further comprise at leastone other different fungicide active ingredient (c).

The fungicidal active ingredient (c) may be selected from azaconazole,azoxystrobin,(Z)-N-[α-(cyclopropylmethoxyimino)-2,3-difluoro-6-(trifluoromethyl)benzyl]-2-phenylacetamide,6-iodo-2-propoxy-3-propylquinazolin-4(3H)-one, benalaxyl, benomyl,benthiavalicarb, biphenyl, bitertanol, blasticidin-S, boscalid, borax,bromuconazole, bupirimate, sec-butylamine, calcium polysulfide,captafol, captan, carbendazim, carboxin, carpropamid, chinomethionat,chlorothalonil, chlozolinate, copper hydroxide, copper octanoate, copperoxychloride, copper sulfate, cuprous oxide, cyazofamid, cymoxanil,cyproconazole, cyprodinil, dazomet, debacarb, dichlofluanid,dichlorophen, diclobutrazole, diclocymet, diclomezine, dicloran,diethofencarb, difenoconazole, difenzoquat metilsulfate, difenzoquat,diflumetorim, dimethirimol, dimethomorph, diniconazole, dinobuton,dinocap, diphenylamine, dithianon, dodemorph, dodemorph acetate, dodine,edifenphos, epoxiconazole, etaconazole, ethaboxam, ethirimol,ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol,fenbuconazole, fenfuram, fenhexamid, fenpiclonil, fenoxanil,fenpropidin, fenpropimorph, fentin, fentin hydroxide, fentin acetate,ferbam, ferimzone, fluazinam, fludioxonil, fluoroimide, fluoxastrobin,fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol,folpet, formaldehyde, fosetyl, fosetyl-aluminium, fuberidazole,furalaxyl, furametpyr, guazatine, guazatine acetates, hexachlorobenzene,hexaconazole, 8-hydroxyquinoline sulfate, potassium hydroxyquinolinesulfate, hymexazol, imazalil sulfate, imazalil, imibenconazole,iminoctadine, iminoctadine triacetate, ipconazole, iprobenfos,iprodione, iprovalicarb, isoprothiolane, kasugamycin, kasugamycinhydrochloride hydrate, kresoxim-methyl, mancopper, mancozeb, maneb,mepanipyrim, mepronil, mercuric chloride, mercuric oxide, mercurouschloride, metalaxyl, metalaxyl-M, metam-sodium, metam, metconazole,methasulfocarb, methyl isothiocyanate, metiram, metominostrobin,mildiomycin, myclobutanil, nabam, nickel bis(dimethyldithiocarbamate),nitrothal-isopropyl, nuarimol, octhilinone, ofurace, oleic acid,oxadixyl, oxine-copper, oxpoconazole fumarate, oxycarboxin, pefurazoate,penconazole, pencycuron, pentachlorophenol, sodium pentachlorophenoxide,pentachlorophenyl laurate, phenylmercury acetate, sodium2-phenylphenoxide, 2-phenylphenol, phosphorous acid, phthalide,picoxystrobin, piperalin, polyoxinspolyoxin B, polyoxin, polyoxorim,probenazole, prochloraz, procymidone, propamocarb hydrochloride,propamocarb, propiconazole, propineb, prothioconazole, pyraclostrobin,pyrazophos, pyributicarb, pyrifenox, pyrimethanil, pyroquilon,quinoxyfen, quintozene, silthiofam, simeconazole, spiroxamine, sulfur,tar oils, tebuconazole, tecnazene, tetraconazole, thiabendazole,thifluzamide, thiophanate-methyl, thiram, tolclofos-methyl,tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole,tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole,validamycin, vinclozolin, zineb, ziram and zoxamide.

Preferably, fungicidal active ingredient (c) is selected fromtrifloxystrobin, fluoxastrobin, pyrimethanil, thiabendazole, guazatine,imidoctadine, picoxystrobin, pyraclostrobin, azoxystrobin,dimoxystrobin, metominostrobin,2-{2-[6-(3-chlor0-2-methylphenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}2-methoxyimino-N-methylacetamide,captane, dodine, propineb, mancozeb, spiroxamine, prothioconazole,tebuconazole, thirame, tolylfluanid, iminoctadine, dithianon, sulphur,copper hydroxide, copper octanoate, copper oxychloride, copper sulfate,dinocap, quinoxyfen, 2-butoxy-6-iodo-3-propyl-benzopyran-4-one,fludioxonil, triazoxide, fosetyl-Al and phosphorous acid.

Where the third active ingredient (c) as defined above is present in thecomposition, this compound may be present in an amount of (a):(b):(c)weight ratio of from 1:0.01:0.01 to 1:20:20; the ratios of compound (a)and compound (c) varying independently from each other. Preferably, the(a):(b):(c) weight ratio may be of from 1:0.05:0.05 to 1:10:10.

Following compositions may be cited to illustrate in a non-limitedmanner the present invention: compound 1 with fenhexamid, compound 1with spiroxamine, compound 1 with triforine, compound 1 withazaconazole, compound 1 with bitertanol, compound 1 with bromuconazole,compound 1 with cyproconazole, compound 1 with difenoconazole, compound1 with diniconazole, compound 1 with epoxiconazole, compound 1 withfenbuconazole, compound 1 with fluquinconazole, compound 1 withflusilazole, compound 1 with flutriafol, compound 1 with hexaconazole,compound 1 with imibenconazole, compound 1 with ipconazole, compound 1with metconazole, compound 1 with myclobutanil, compound 1 withpenconazole, compound 1 with propiconazole, compound 1 withprothioconazole, compound 1 with simeconazole, compound 1 withtebuconazole, compound 1 with tetraconazole, compound 1 withtriadimefon, compound 1 with triadimenol, compound 1 with triticonazole,compound 1 with diclobutrazole, compound 1 with etaconazole, compound 1with fluotrimazole, compound 1 with furconazole, compound 1 withfurconazole-cis, compound 1 with triamiphos, compound 1 with triazbutil,compound 1 with imazalil, compound 1 with prochloraz, compound 1 withoxpoconazole fumarate, compound 1 with pefurazoate, compound 1 withtriflumizole, compound 1 with aldimorph, compound 1 with dodemorph,compound 1 with fenpropimorph, compound 1 with tridemorph, compound 1with fenpropidin, compound 1 with piperalin, compound 2 with fenhexamid,compound 2 with spiroxamine, compound 2 with triforine, compound 2 withazaconazole, compound 2 with bitertanol, compound 2 with bromuconazole,compound 2 with cyproconazole, compound 2 with difenoconazole, compound2 with diniconazole, compound 2 with epoxiconazole, compound 2 withfenbuconazole, compound 2 with fluquinconazole, compound 2 withflusilazole, compound 2 with flutriafol, compound 2 with hexaconazole,compound 2 with imibenconazole, compound 2 with ipconazole, compound 2with metconazole, compound 2 with myclobutanil, compound 2 withpenconazole, compound 2 with propiconazole, compound 2 withprothioconazole, compound 2 with simeconazole, compound 2 withtebuconazole, compound 2 with tetraconazole, compound 2 withtriadimefon, compound 2 with triadimenol, compound 2 with triticonazole,compound 2 with diclobutrazole, compound 2 with etaconazole, compound 2with fluotrimazole, compound 2 with furconazole, compound 2 withfurconazole-cis, compound 2 with triamiphos, compound 2 with triazbutil,compound 2 with imazalil, compound 2 with prochloraz, compound 2 withoxpoconazole fumarate, compound 2 with pefurazoate, compound 2 withtriflumizole, compound 2 with aldimorph, compound 2 with dodemorph,compound 2 with fenpropimorph, compound 2 with tridemorph, compound 2with fenpropidin, compound 2 with piperalin, compound 3 with fenhexamid,compound 3 with spiroxamine, compound 3 with triforine, compound 3 withazaconazole, compound 3 with bitertanol, compound 3 with bromuconazole,compound 3 with cyproconazole, compound 3 with difenoconazole, compound3 with diniconazole, compound 3 with epoxiconazole, compound 3 withfenbuconazole, compound 3 with fluquinconazole, compound 3 withflusilazole, compound 3 with flutriafol, compound 3 with hexaconazole,compound 3 with imibenconazole, compound 3 with ipconazole, compound 3with metconazole, compound 3 with myclobutanil, compound 3 withpenconazole, compound 3 with propiconazole, compound 3 withprothioconazole, compound 3 with simeconazole, compound 3 withtebuconazole, compound 3 with tetraconazole, compound 3 withtriadimefon, compound 3 with triadimenol, compound 3 with triticonazole,compound 3 with diclobutrazole, compound 3 with etaconazole, compound 3with fluotrimazole, compound 3 with furconazole, compound 3 withfurconazole-cis, compound 3 with triamiphos, compound 3 with triazbutil,compound 3 with imazalil, compound 3 with prochloraz, compound 3 withoxpoconazole fumarate, compound 3 with pefurazoate, compound 3 withtriflumizole, compound 3 with aldimorph, compound 3 with dodemorph,compound 3 with fenpropimorph, compound 3 with tridemorph, compound 3with fenpropidin, compound 3 with piperalin.

The composition according to the present invention may further comprisean other additional component such as an agriculturally acceptablesupport, carrier or filler.

In the present specification, the term “support” denotes a natural orsynthetic, organic or inorganic material with which the active materialis combined to make it easier to apply, notably to the parts of theplant. This support is thus generally inert and should be agriculturallyacceptable. The support may be a solid or a liquid. Examples of suitablesupports include clays, natural or synthetic silicates, silica, resins,waxes, solid fertilisers, water, alcohols, in particular butanol,organic solvents, mineral and plant oils and derivatives thereof.Mixtures of such supports may also be used.

The composition may also comprise other additional components. Inparticular, the composition may further comprise a surfactant. Thesurfactant can be an emulsifier, a dispersing agent or a wetting agentof ionic or non-ionic type or a mixture of such surfactants. Mention maybe made, for example, of polyacrylic acid salts, lignosulphonic acidsalts, phenolsulphonic or naphthalenesulphonic acid salts,polycondensates of ethylene oxide with fatty alcohols or with fattyacids or with fatty amines, substituted phenols (in particularalkylphenols or arylphenols), salts of sulphosuccinic acid esters,taurine derivatives (in particular alkyl taurates), phosphoric esters ofpolyoxyethylated alcohols or phenols, fatty acid esters of polyols, andderivatives of the above compounds containing sulphate, sulphonate andphosphate functions. The presence of at least one surfactant isgenerally essential when the active material and/or the inert supportare water-insoluble and when the vector agent for the application iswater. Preferably, surfactant content may be comprised between 5% and40% by weight of the composition.

Additional components may also be included, e.g. protective colloids,adhesives, thickeners, thixotropic agents, penetration agents,stabilisers, sequestering agents. More generally, the active materialscan be combined with any solid or liquid additive, which complies withthe usual formulation techniques.

In general, the composition according to the invention may contain from0.05 to 99% (by weight) of active material, preferably 10 to 70% byweight.

Compositions according to the present invention can be used in variousforms such as aerosol dispenser, capsule suspension, cold foggingconcentrate, dustable powder, emulsifiable concentrate, emulsion oil inwater, emulsion water in oil, encapsulated granule, fine granule,flowable concentrate for seed treatment, gas (under pressure), gasgenerating product, granule, hot fogging concentrate, macrogranule,microgranule, oil dispersible powder, oil miscible flowable concentrate,oil miscible liquid, paste, plant rodlet, powder for dry seed treatment,seed coated with a pesticide, soluble concentrate, soluble powder,solution for seed treatment, suspension concentrate (flowableconcentrate), ultra low volume (ulv) liquid, ultra low volume (ulv)suspension, water dispersible granules or tablets, water dispersiblepowder for slurry treatment, water soluble granules or tablets, watersoluble powder for seed treatment and wettable powder.

These compositions include not only compositions which are ready to beapplied to the plant or seed to be treated by means of a suitabledevice, such as a spraying or dusting device, but also concentratedcommercial compositions which must be diluted before they are applied tothe crop.

The fungicidal compositions of the present invention can be used tocuratively or preventively control phytopathogenic fungi of crops. Thus,according to a further aspect of the present invention, there isprovided a method for preventively or curatively controllingphytopathogenic fungi of crops characterised in that a fungicidalcomposition as hereinbefore defined is applied to the seed, the plantand/or to the fruit of the plant or to the soil in which the plant isgrowing or in which it is desired to grow.

The composition as used against phytopathogenic fungi of crops comprisesan effective and non-phytotoxic amount of an active material of generalformula (I).

The expression “effective and non-phytotoxic amount” means an amount ofcomposition according to the invention which is sufficient to control ordestroy the fungi present or liable to appear on the crops, and whichdoes not entail any appreciable symptom of phytotoxicity for the saidcrops. Such an amount can vary within a wide range depending on thefungus to be combated or controlled, the type of crop, the climaticconditions and the compounds included in the fungicidal compositionaccording to the invention.

This amount can be determined by systematic field trials, which arewithin the capabilities of a person skilled in the art.

The method of treatment according to the present invention is useful totreat propagation material such as tubers or rhizomes, but also seeds,seedlings or seedlings pricking out and plants or plants pricking out.This method of treatment can also be useful to treat roots. The methodof treatment according to the present invention can also be useful totreat the overground parts of the plant such as trunks, stems or stalks,leaves, flowers and fruits of the concerned plant.

Among the plants that can be protected by the method according to theinvention, mention may be made of cotton; flax; vine; fruit crops suchas Rosaceae sp. (for instance pip fruits such as apples and pears, butalso stone fruits such as apricots, almonds and peaches), Ribesioidaesp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp.,Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceaesp. (for instance banana trees and plantins), Rubiaceae sp., Theaceaesp., Sterculiceae sp., Rutaceae sp. (for instance lemons, oranges andgrapefruits); leguminous crops such as Solanaceae sp. (for instancetomatoes), Liliaceae sp., Asteraceae sp. (for instance lettuces),Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp.,Papilionaceae sp. (for instance peas), Rosaceae sp. (for instancestrawberries); big crops such as Graminae sp. (for instance maize,cereals such as wheat, rice, barley and triticale), Asteraceae sp. (forinstance sunflower), Cruciferae sp. (for instance colza), Papilionaceaesp. (for instance soj a), Solanaceae sp. (for instance potatoes),Chenopodiaceae sp. (for instance beetroots); horticultural and forestcrops; as well as genetically modified homologues of these crops.

Among the plants and the possible diseases of these plants protected bythe method according to the present invention, mention may be made of:

-   -   wheat, as regards controlling the following seed diseases:        fusaria (Microdochium nivale and Fusarium roseum), stinking smut        (Tilletia caries, Tilletia controversa or Tilletia indica),        septoria disease (Septoria nodorum) and loose smut;    -   wheat, as regards controlling the following diseases of the        aerial parts of the plant: cereal eyespot (Tapesia yallundae,        Tapesia acuiformis), take-all (Gaeumannomyces graminis), foot        blight (F. culmorum, F. graminearum), black speck (Rhizoctonia        cerealis), powdery mildew (Erysiphe graminis forma specie        tritici), rusts (Puccinia striiformis and Puccinia recondita)        and septoria diseases (Septoria tritici and Septoria nodorum);    -   wheat and barley, as regards controlling bacterial and viral        diseases, for example barley yellow mosaic;    -   barley, as regards controlling the following seed diseases: net        blotch (Pyrenophora graminea, Pyrenophora teres and Cochliobolus        sativus), loose smut (Ustilago nuda) and fusaria (Microdochium        nivale and Fusarium roseum);    -   barley, as regards controlling the following diseases of the        aerial parts of the plant: cereal eyespot (Tapesia yallundae),        net blotch (Pyrenophora teres and Cochliobolus sativus), powdery        mildew (Erysiphe graminis forma specie hordei), dwarf leaf rust        (Puccinia hordei) and leaf blotch (Rhynchosporium secalis);    -   potato, as regards controlling tuber diseases (in particular        Helminthosporium solani, Phoma tuberosa, Rhizoctonia solani,        Fusarium solani), mildew (Phytopthora infestans) and certain        viruses (virus Y);    -   potato, as regards controlling the following foliage diseases:        early blight (Alternaria solani), mildew (Phytophthora        infestans);    -   cotton, as regards controlling the following diseases of young        plants grown from seeds: damping-off and collar rot (Rhizoctonia        solani, Fusarium oxysporum) and black root rot (Thielaviopsis        basicola);    -   protein yielding crops, for example peas, as regards controlling        the following seed diseases: anthracnose (Ascochyta pisi,        Mycosphaerella pinodes), fusaria (Fusarium oxysporum), grey        mould (Botrytis cinerea) and mildew (Peronospora pisi);    -   oil-bearing crops, for example rape, as regards controlling the        following seed diseases: Phoma lingam, Alternaria brassicae and        Sclerotinia sclerotiorum;    -   corn, as regards controlling seed diseases: (Rhizopus sp.,        Penicillium sp., Trichoderma sp., Aspergillus sp., and        Gibberella fujikuroi);    -   flax, as regards controlling the seed disease: Alternaria        linicola;    -   forest trees, as regards controlling damping-off (Fusarium        oxysporum, Rhizoctonia solani);    -   rice, as regards controlling the following diseases of the        aerial parts: blast disease (Magnaporthe grisea), bordered        sheath spot (Rhizoctonia solani);    -   leguminous crops, as regards controlling the following diseases        of seeds or of young plants grown from seeds: damping-off and        collar rot (Fusarium oxysporum, Fusarium roseum, Rhizoctonia        solani, Pythium sp.);    -   leguminous crops, as regards controlling the following diseases        of the aerial parts: grey mould (Botrytis sp.), powdery mildews        (in particular Erysiphe cichoracearum, Sphaerotheca fuliginea        and Leveillula taurica), fusaria (Fusarium oxysporum, Fusarium        roseum), leaf spot (Cladosporium sp.), alternaria leaf spot        (Alternaria sp.), anthracnose (Colletotrichum sp.), septoria        leaf spot (Septoria sp.), black speck (Rhizoctonia solani),        mildews (for example Bremia lactucae, Peronospora sp.,        Pseudoperonospora sp., Phytophthora sp.);    -   fruit trees, as regards diseases of the aerial parts: monilia        disease (Monilia fructigenae, M. laxa), scab (Venturia        inaequalis), powdery mildew (Podosphaera leucotricha);    -   vine, as regards diseases of the foliage: in particular grey        mould (Botrytis cinerea), powdery mildew (Uncinula necator),        black rot (Guignardia biwelli) and mildew (Plasmopara viticola);    -   beetroot, as regards the following diseases of the aerial parts:        cercospora blight (Cercospora beticola), powdery mildew        (Erysiphe beticola), leaf spot (Ramularia beticola).

The fungicidal composition according to the present invention may alsobe used against fungal diseases liable to grow on or inside timber. Theterm “timber” means all types of species of wood, and all types ofworking of this wood intended for construction, for example solid wood,high-density wood, laminated wood, and plywood. The method for treatingtimber according to the invention mainly consists in contacting one ormore compounds of the present invention, or a composition according tothe invention; this includes for example direct application, spraying,dipping, injection or any other suitable means.

The fungicidal composition according to the present invention may alsobe used in the treatment of genetically modified organisms with thecompounds according to the invention or the agrochemical compositionsaccording to the invention. Genetically modified plants are plants intoin which genome a heterologous gene encoding a protein of interest hasbeen stably integrated. The expression “heterologous gene encoding aprotein of interest” essentially means genes which give the transformedplant new agronomic properties, or genes for improving the agronomicquality of the transformed plant.

The dose of active material usually applied in the treatment accordingto the present invention is generally and advantageously between 10 and2000 g/ha, preferably between 20 and 1500 g/ha for applications infoliar treatment. The dose of active substance applied is generally andadvantageously between 1 and 200 g per 100 kg of seed, preferablybetween 2 and 150 g per 100 kg of seed in the case of seed treatment. Itis clearly understood that the doses indicated above are given asillustrative examples of the invention. A person skilled in the art willknow how to adapt the application doses according to the nature of thecrop to be treated.

The compositions according to the present invention may also be usedfore the preparation of composition useful to curatively or preventivelytreat human and animal fungal diseases such as, for example, mycoses,dermatoses, trichophyton diseases and candidiases or diseases caused byAspergillus spp. or Candida spp., for example Aspergillus fumigatus orCandida albicans respectively.

The present invention will now be illustrated with the followingexample:

EXAMPLE 1: EFFICACY AGAINST MYCOSPHAERELLA GRAMINICOLA OF A MIXTURECONTAININGN-{2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ETHYL}-2-TRIFLUOROMETHYL-BENZAMIDE(COMPOUND 1) AND TEBUCONAZOLE

The active ingredients tested are prepared by potter homogenisation in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Wheat plants (Scipion variety), sown on a 50/50 peat soil-pozzolanasubstrate in starter cups and grown at 12° C., are treated at the 1-leafstage (10 cm tall) by spraying with the aqueous suspension describedabove. Plants, used as controls, are treated with an aqueous solutionnot containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Mycosphaerella graminicola spores (500 000 sporesper ml). The spores are collected from a 7-day-old culture. Thecontaminated wheat plants are incubated for 72 hours at 18° C. and at100% relative humidity, and then for 21 to 28 days at 90% relativehumidity.

Grading (% of efficacy) is carried out 21 to 28 days after thecontamination, in comparison with the control plants.

The following table summarises the results obtained when tested compound1 and tebuconazole alone and in a 1/1 weight ratio mixture.

Dose Synergism (g/ha) % Efficacy (Colby) Compound 1 15 25 — 31 65 —Tebuconazole 15 15 — 31 15 — Compound 1 + tebuconazole 15 + 15 75 +39(Ratio 1/1) 31 + 31 80 +10

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 2: EFFICACY AGAINST ERYSIPHE GRAMINIS F. SP. GRAMINIS OF AMIXTURE CONTAININGN-{2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ETHYL}-2-TRIFLUOROMETHYLBENZAMIDE(COMPOUND 1) AND PROTHIOCONAZOLE

The active ingredients tested are prepared by potter homogenisation in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Wheat plants (Audace variety) in starter cups, sown on 50/50 peatsoil-pozzolana substrate and grown at 12° C., are treated at the 1-leafstage (10 cm tall) by spraying with the aqueous suspension describedabove.

Plants, used as controls, are treated with an aqueous solution notcontaining the active material.

After 24 hours, the plants are contaminated by dusting them withErysiphe graminis f sp. tritici spores, the dusting being carried outusing diseased plants.

Grading is carried out 7 to 14 days after the contamination, incomparison with the control plants.

The following table summarises the results obtained when tested compound1 and prothioconazole alone and in a 1/2 weight ratio mixture.

Dose Synergism (g/ha) % Efficacy (Colby) Compound 1 125 20 — 62.5 0 —Prothioconazole 250 60 — 125 0 — Compound 1 + prothioconazole 125 + 25085 +17 (Ratio 1/2)  62 + 125 70 +70

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 3: EFFICACY AGAINST BOTRYTIS CINEREA OF A MIXTURE CONTAININGN-{2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ETHYL}-2-TRIFLUOROMETHYLBENZAMIDE(COMPOUND 1) AND PROPICONAZOLE

The active ingredients tested are prepared by potter homogenisation in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 18-20° C., are treatedat the cotyledon Z11 stage by spraying with the aqueous suspensiondescribed above. Plants, used as controls, are treated with an aqueoussolution not containing the active material.

After 24 hours, the plants are contaminated by depositing drops of anaqueous suspension of Botrytis cinerea spores (150,000 spores per ml) onupper surface of the leaves. The spores are collected from a 15-day-oldculture and are suspended in a nutrient solution composed of:

-   -   20 g/L of gelatine    -   50 g/L of cane sugar    -   2 g/L of NH4NO3    -   1 g/L of KH2PO4

The contaminated gherkin plants are settled for 5/7 days in a climaticroom at 15-11° C. (day/night) and at 80% relative humidity. Grading (%of efficacy) is carried out 5 to 7 days after the contamination, incomparison with the control plants.

The following table summarises the results obtained when tested compound1 and propiconazole alone and in different weight ratio mixtures.

Dose Synergism (ppm) % Efficacy (Colby) Compound 1 12 0 — 37 30 — 111 80— Propiconazole 37 30 — 111 50 — 333 70 — Compound 1 + propiconazole37 + 333 100 21 (Ratio 1/9) 12 + 111 100 50 Compound 1 + propiconazole37 + 111 100 +35 (Ratio 1/3) Compound 1 + propiconazole 37 + 37  80 +29(Ratio 1/1)

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 4: EFFICACY AGAINST ERYSIPHE GRAMINIS F. SP. GRAMINIS OF AMIXTURE CONTAININGN-{2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ETHYL}-2-TRIFLUOROMETHYLBENZAMIDE(COMPOUND 1) AND CYPROCONAZOLE

The formulated (concentrated suspension) compounds are diluted withwater to obtain the desired active material concentration Wheat plants(Audace variety) in starter cups, sown on 50/50 peat soil-pozzolanasubstrate and grown at 12° C., are treated at the 1-leaf stage (10 cmtall) by spraying with the aqueous suspension described above.

Plants, used as controls, are treated with an aqueous solution notcontaining the active material.

After 24 hours, the plants are contaminated by dusting them withErysiphe graminis f sp. tritici spores, the dusting being carried outusing diseased plants.

Grading is carried out 7 to 14 days after the contamination, incomparison with the control plants.

The following table summarises the results obtained when tested compound1 and cyproconazole alone and in a 2/1 weight ratio mixture.

Dose Synergism (g/ha) % Efficacy (Colby) Compound 1 62.5 10 —Cyproconazole 31.2 15 — Compound 1 + cyproconazole 62.5 + 31.2 60 +37(Ratio 2/1)

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 5: EFFICACY AGAINST BOTRYTIS CINEREA OF A MIXTURE CONTAININGN-{2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ETHYL}-2-TRIFLUOROMETHYLBENZAMIDECOMPOUND 1) AND DIFENCONAZOLE

The active ingredients tested are prepared by potter homogenisation in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 18-20° C., are treatedat the cotyledon Z11 stage by spraying with the aqueous suspensiondescribed above. Plants, used as controls, are treated with an aqueoussolution not containing the active material.

After 24 hours, the plants are contaminated by depositing drops of anaqueous suspension of Botrytis cinerea spores (150,000 spores per ml) onupper surface of the leaves. The spores are collected from a 15-day-oldculture and are suspended in a nutrient solution composed of:

-   -   20 g/L of gelatine    -   50 g/L of cane sugar    -   2 g/L of NH4NO3    -   1 g/L of KH2PO4

The contaminated gherkin plants are settled for 5/7 days in a climaticroom at 15-11° C. (day/night) and at 80% relative humidity. Grading (%of efficacy) is carried out 5 to 7 days after the contamination, incomparison with the control plants.

The following table summarises the results obtained when tested compound1 and difenconazole alone and in different weight ratio mixtures.

Dose Synergism (ppm) % Efficacy (Colby) Compound 1 37 0 — 111 80 —Difenconazole 111 15 — 333 25 — Compound 1 + difenconazole  37 + 111 80+65 (Ratio 1/3) Compound 1 + difenconazole 111 + 111 100 +17 (Ratio 1/1)Compound 1 + difenconazole 111 + 333 80 +55 (Ratio 1/9)

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 6: EFFICACY AGAINST BOTRYTIS CINEREA OF A MIXTURE CONTAININGN-{2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ETHYL}-2-TRIFLUOROMETHYLBENZAMIDE(COMPOUND 1) AND HEXACONAZOLE

The active ingredients tested are prepared by potter homogenisation in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 18-20° C., are treatedat the cotyledon Z11 stage by spraying with the aqueous suspensiondescribed above. Plants, used as controls, are treated with an aqueoussolution not containing the active material.

After 24 hours, the plants are contaminated by depositing drops of anaqueous suspension of Botrytis cinerea spores (150,000 spores per ml) onupper surface of the leaves. The spores are collected from a 15-day-oldculture and are suspended in a nutrient solution composed of:

-   -   20 g/L of gelatine    -   50 g/L of cane sugar    -   2 g/L of NH4NO3    -   1 g/L of KH2PO4

The contaminated gherkin plants are settled for 5/7 days in a climaticroom at 15-11° C. (day/night) and at 80% relative humidity. Grading (%of efficacy) is carried out 5 to 7 days after the contamination, incomparison with the control plants.

The following table summarises the results obtained when tested compound1 and hexaconazole alone and in a 1:27 weight ratio mixture.

Dose Synergism (ppm) % Efficacy (Colby) Compound 1 4 10 — Hexaconazole111 15 — Compound 1 + hexaconazole 4 + 111 98 +19 (Ratio 1:27)

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 7: EFFICACY AGAINST ERYSIPHE GRAMINIS F. SP. GRAMINIS OF AMIXTURE CONTAININGN-{2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ETHYL}-2-TRIFLUOROMETHYLBENZAMIDE(COMPOUND 1) AND METCONAZOLE

The formulated compounds are diluted with water to obtain the desiredactive material concentration. Wheat plants (Audace variety) in startercups, sown on 50/50 peat soil-pozzolana substrate and grown at 12° C.,are treated at the 1-leaf stage (10 cm tall) by spraying with theaqueous suspension described above.

Plants, used as controls, are treated with an aqueous solution notcontaining the active material.

After 24 hours, the plants are contaminated by dusting them withErysiphe graminis f sp. tritici spores, the dusting being carried outusing diseased plants. Grading is carried out 7 to 14 days after thecontamination, in comparison with the control plants.

The following table summarises the results obtained when tested compound1 and metconazole alone and in a 8:1 weight ratio mixture.

Dose Synergism (g/ha) % Efficacy (Colby) Compound 1 250 40 — Metconazole31.2 50 — Compound 1 + metconazole 250 + 31.2 80 +10 (Ratio 8:1)

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 8: EFFICACY AGAINST PUCCINIA RECONDITA OF A MIXTURE CONTAININGN-{2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ETHYL}-2-TRIFLUOROMETHYLBENZAMIDE(COMPOUND 1) AND EPOXICONAZOLE

The formulated compounds are diluted with water to obtain the desiredactive material concentration Wheat plants (Scipion variety) in startercups, sown on 50/50 peat soil-pozzolana substrate and grown at 12° C.,are treated at the 1-leaf stage (10 cm tall) by spraying with theaqueous suspension described above.

Plants, used as controls, are treated with an aqueous solution notcontaining the active material.

After 24 hours, the plants are contaminated by spraying the leaves withan aqueous suspension of Puccinia recondita spores (100,000 spores perml). The spores are collected from a 10-day-old contaminated wheat andare suspended in water containing 2.5 ml/l of tween 80 10%. Thecontaminated wheat plants are incubated for 24 hours at 20° C. and at100% relative humidity, and then for 10 days at 20° C. and at 70%relative humidity. Grading is carried out 10 days after thecontamination, in comparison with the control plants.

The following table summarises the results obtained when tested compound1 and epoxiconazole alone and in different weight ratio mixtures.

Dose Synergism (g/ha) % Efficacy (Colby) Compound 1 62.5 0 — 250 0 —Epoxiconazole 15.6 25 — Compound 1 + epoxiconazole  250 + 15.6 80 +55(Ratio 16:1) Compound 1 + epoxiconazole 62.5 + 15.6 85 +60 (Ratio 4:1)

According to the Colby method, a synergistic effect of the mixturestested has been observed

EXAMPLE 9: EFFICACY AGAINST BOTRYTIS CINEREA OF A MIXTURE CONTAININGN-{2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ETHYL}-2-TRIFLUOROMETHYLBENZAMIDE(COMPOUND 1) AND MYCLOBUTANIL

The formulated compounds are diluted with water to obtain the desiredactive material concentration.

Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 18-20° C., are treatedat the cotyledon Z11 stage by spraying with the aqueous suspensiondescribed above. Plants, used as controls, are treated with an aqueoussolution not containing the active material.

After 24 hours, the plants are contaminated by depositing drops of anaqueous suspension of Botrytis cinerea spores (150,000 spores per ml) onupper surface of the leaves. The spores are collected from a 15-day-oldculture and are suspended in a nutrient solution composed of:

-   -   20 g/L of gelatine    -   50 g/L of cane sugar    -   2 g/L of NH4NO3    -   1 g/L of KH2PO4

The contaminated gherkin plants are settled for 5/7 days in a climaticroom at 15-11° C. (day/night) and at 80% relative humidity. Grading (%of efficacy) is carried out 5 to 7 days after the contamination, incomparison with the control plants.

The following table summarises the results obtained when tested compound1 and myclobutanil alone and in different weight ratio mixtures.

Dose Synergism (ppm) % Efficacy (Colby) Compound 1 12.3 0 — 37 50 —Myclobutanil 333 0 — Compound 1 + myclobutanil 12.3 + 333 53 +53 (Ratio1:27) Compound 1 + myclobutanil   37 + 333 70 +20 (Ratio 1:9)

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 10: EFFICACY AGAINST PUCCINIA RECONDITA OF A MIXTURE CONTAININGN-{2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ETHYL}-2-TRIFLUOROMETHYLBENZAMIDE(COMPOUND 1) AND TRIADIMENOL

The active ingredients tested are prepared by potter homogenisation in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Wheat plants (Scipion variety) in starter cups, sown on 50/50 peatsoil-pozzolana substrate and grown at 12° C., are treated at the 1-leafstage (10 cm tall) by spraying with the aqueous suspension describedabove.

Plants, used as controls, are treated with an aqueous solution notcontaining the active material.

After 24 hours, the plants are contaminated by spraying the leaves withan aqueous suspension of Puccinia recondita spores (100,000 spores perml). The spores are collected from a 10-day-old contaminated wheat andare suspended in water containing 2.5 ml/l of tween 80 10%. Thecontaminated wheat plants are incubated for 24 hours at 20° C. and at100% relative humidity, and then for 10 days at 20° C. and at 70%relative humidity. Grading is carried out 10 days after thecontamination, in comparison with the control plants.

The following table summarises the results obtained when tested compound1 and triadimenol alone and in a 1:1 weight ratio mixture.

Dose Synergism (g/ha) % Efficacy (Colby) Compound 1 250 0 — Triadimenol250 50 — Compound 1 + triadimenol 250 + 250 70 +20 (Ratio 1:1)

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 11: EFFICACY AGAINST SPHAEROTHECA FULIGINEA OF A COMPOSITIONCONTAININGN-{2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ETHYL}-2-TRIFLUOROMETHYL-BENZAMIDE(COMPOUND 1) AND FENHEXAMID

The formulated compounds are diluted with water to obtain the desiredactive material concentration

Gherkin plants (Vert petit de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 20° C./23° C., aretreated at the 2-leaves stage by spraying with the aqueous suspensiondescribed above. Plants, used as controls, are treated with an aqueoussolution not containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Sphaerotheca fuliginea spores (100 000 spores perml). The spores are collected from a contaminated plants. Thecontaminated gerkhin plants are incubated at about 20° C./25° C. and at60/70% relative humidity.

Grading (% of efficacy) is carried out 21 days after the contamination,in comparison with the control plants.

The following table summarises the results obtained when tested compound1 and fenhexamid alone and in a 1:9 weight ratio mixture.

Dose Synergism (ppm) % Efficacy (Colby) Compound 1 4.1 28 — Fenhexamid37 35 — Compound 1 + fenhexamid 4.1 + 37 74 +21 (Ratio 1:9)

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 12: EFFICACY AGAINST MYCOSPHAERELLA GRAMINICOLA OF A MIXTURECONTAININGN-{2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ETHYL}-2-TRIFLUOROMETHYLBENZAMIDE(COMPOUND 1) AND PROCHLORAZ

The formulated compounds are diluted with water to obtain the desiredactive material concentration

Wheat plants (Scipion variety), sown on a 50/50 peat soil-pozzolanasubstrate in starter cups and grown at 12° C., are treated at the 1-leafstage (10 cm tall) by spraying with the aqueous suspension describedabove. Plants, used as controls, are treated with an aqueous solutionnot containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Mycosphaerella graminicola spores (500 000 sporesper ml). The spores are collected from a 7-day-old culture. Thecontaminated wheat plants are incubated for 72 hours at 18° C. and at100% relative humidity, and then for 21 to 28 days at 90% relativehumidity.

Grading (% of efficacy) is carried out 21 to 28 days after thecontamination, in comparison with the control plants.

The following table summarises the results obtained when tested compound1 and prochloraz alone and in a 1:4 weight ratio mixture.

Dose Synergism (g/ha) % Efficacy (Colby) Compound 1 62.5 77 — Prochloraz250 54 — Compound 1 + Prochloraz 62.5 + 250 98 +9 (Ratio 1/4)

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 13: EFFICACY AGAINST BOTRYTIS CINEREA OF A MIXTURE CONTAININGN-{2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ETHYL}-2-TRIFLUOROMETHYLBENZAMIDE(COMPOUND 1) AND FENPROPIMORPH

The formulated compounds are diluted with water to obtain the desiredactive material concentration.

Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 18-20° C., are treatedat the cotyledon Z11 stage by spraying with the aqueous suspensiondescribed above. Plants, used as controls, are treated with an aqueoussolution not containing the active material.

After 24 hours, the plants are contaminated by depositing drops of anaqueous suspension of Botrytis cinerea spores (150,000 spores per ml) onupper surface of the leaves. The spores are collected from a 15-day-oldculture and are suspended in a nutrient solution composed of:

-   -   20 g/L of gelatine    -   50 g/L of cane sugar    -   2 g/L of NH4NO3    -   1 g/L of KH2PO4

The contaminated gherkin plants are settled for 5/7 days in a climaticroom at 15-11° C. (day/night) and at 80% relative humidity. Grading (%of efficacy) is carried out 5 to 7 days after the contamination, incomparison with the control plants.

The following table summarises the results obtained when tested compound1 and fenpropimorph alone and in 1:2 weight ratio mixture.

Dose Synergism (g/ha) % Efficacy (Colby) Compound 1 31.2 20 — 62.5 30 —Fenpropimorph 62.5 10 — 125 30 — Compound 1 + fenpropimorph 31.2 + 62.560 +32 (Ratio 1:2) 62.5 + 125  80 +29

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 14: EFFICACY AGAINST ERYSIPHE GRAMINIS F. SP. GRAMINIS OF AMIXTURE CONTAININGN-{2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ETHYL}-2-TRIFLUOROMETHYLBENZAMIDE(COMPOUND 1) AND SPIROXAMINE

The formulated compounds are diluted with water to obtain the desiredactive material concentration Wheat plants (Audace variety) in startercups, sown on 50/50 peat soil-pozzolana substrate and grown at 12° C.,are treated at the 1-leaf stage (10 cm tall) by spraying with theaqueous suspension described above.

Plants, used as controls, are treated with an aqueous solution notcontaining the active material.

After 24 hours, the plants are contaminated by dusting them withErysiphe graminis f sp. tritici spores, the dusting being carried outusing diseased plants.

Grading is carried out 7 to 14 days after the contamination, incomparison with the control plants.

The following table summarises the results obtained when tested compound1 and spiroxamine alone and in a 4:1 weight ratio mixture.

Dose Synergism (g/ha) % Efficacy (Colby) Compound 1 500 44 — Spiroxamine125 0 — Compound 1 + spiroxamine 500 + 125 72 +28 (Ratio 4:1)

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 15: EFFICACY AGAINST BOTRYTIS CINEREA OF A MIXTURE CONTAININGN-{2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ETHYL}-2-TRIFLUOROMETHYLBENZAMIDE(COMPOUND 1) AND TRIFORINE

The formulated compounds are diluted with water to obtain the desiredactive material concentration.

Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 18-20° C., are treatedat the cotyledon Z11 stage by spraying with the aqueous suspensiondescribed above. Plants, used as controls, are treated with an aqueoussolution not containing the active material.

After 24 hours, the plants are contaminated by depositing drops of anaqueous suspension of Botrytis cinerea spores (150,000 spores per ml) onupper surface of the leaves. The spores are collected from a 15-day-oldculture and are suspended in a nutrient solution composed of:

-   -   20 g/L of gelatine    -   50 g/L of cane sugar    -   2 g/L of NH4NO3    -   1 g/L of KH2PO4

The contaminated gherkin plants are settled for 5/7 days in a climaticroom at 15-11° C. (day/night) and at 80% relative humidity. Grading (%of efficacy) is carried out 5 to 7 days after the contamination, incomparison with the control plants.

The following table summarises the results obtained when tested compound1 and triforine alone and in different weight ratio mixtures.

Dose Synergism (ppm) % Efficacy (Colby) Compound 1 37 50 — Triforine 370 — 111 15 — Compound 1 + triforine 37 + 37  65 +15 (Ratio 1:1) Compound1 + triforine 37 + 111 70 +13 (Ratio 1:3)

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 16: EFFICACY AGAINST BOTRYTIS CINEREA OF A MIXTURE CONTAININGN-{2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ETHYL}-2-TRIFLUOROMETHYLBENZAMIDE(COMPOUND 1) AND BITERTANOL

The formulated compounds are diluted with water to obtain the desiredactive material concentration.

Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 18-20° C., are treatedat the cotyledon Z11 stage by spraying with the aqueous suspensiondescribed above. Plants, used as controls, are treated with an aqueoussolution not containing the active material.

After 24 hours, the plants are contaminated by depositing drops of anaqueous suspension of Botrytis cinerea spores (150,000 spores per ml) onupper surface of the leaves. The spores are collected from a 15-day-oldculture and are suspended in a nutrient solution composed of:

-   -   20 g/L of gelatine    -   50 g/L of cane sugar    -   2 g/L of NH4NO3    -   1 g/L of KH2PO4

The contaminated gherkin plants are settled for 5/7 days in a climaticroom at 15-11° C. (day/night) and at 80% relative humidity. Grading (%of efficacy) is carried out 5 to 7 days after the contamination, incomparison with the control plants.

The following table summarises the results obtained when tested compound1 and bitertanol alone and in a 1:9 weight ratio mixture.

Dose Synergism (ppm) % Efficacy (Colby) Compound 1 12.3 5 — Bitertanol333 0 — Compound 1 + bitertanol 12.3 + 333 95 +90 (Ratio 1:9)

According to the Colby method, a synergistic effect of the mixturetested has been observed.

EXAMPLE 17: EFFICACY AGAINST ERYSIPHE GRAMINIS F. SP. GRAMINIS OF AMIXTURE CONTAININGN-{2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ETHYL}-2-TRIFLUOROMETHYLBENZAMIDE(COMPOUND 1), SPIROXAMINE AND PROTHIOCONAZOLE

The formulated compounds (Compound 1 and a mix of spiroxamine (300 g/l)and prothioconazole (160 g/l) are diluted with water to obtain thedesired active material concentration Wheat plants (Audace variety) instarter cups, sown on 50/50 peat soil-pozzolana substrate and grown at12° C., are treated at the 1-leaf stage (10 cm tall) by spraying withthe aqueous suspension described above.

Plants, used as controls, are treated with an aqueous solution notcontaining the active material.

After 24 hours, the plants are contaminated by dusting them withErysiphe graminis f sp. tritici spores, the dusting being carried outusing diseased plants.

Grading is carried out 7 to 14 days after the contamination, incomparison with the control plants.

The following table summarises the results obtained when tested compound1 and the mix of spiroxamine and prothioconazole alone and in a 8:1weight ratio mixture.

Dose Synergism (g/ha) % Efficacy (Colby) Compound 1 125 0 —Spiroxamine + 15.6 45 — prothioconazole Compound 1 + spiroxamine + 125 +15.6 95 +50 prothioconazole (Ratio 8:1)According to the Colby method, a synergistic effect of the mixturestested has been observed.

The invention claimed is:
 1. A composition comprising a) apyridylethylbenzamide derivative of formula (I)

or 2-pyridine N-oxides thereof, in which p is an integer equal to 1, 2,3 or 4; q is an integer equal to 1, 2, 3, 4 or 5; each substituent X,independently of the others, is halogen, alkyl or haloalkyl; eachsubstituent Y, independently of the others, is halogen, alkyl, alkenyl,alkynyl, haloalkyl, alkoxy, amino, phenoxy, alkylthio, dialkylamino,acyl, cyano, ester, hydroxy, aminoalkyl, benzyl, haloalkoxy,halosulphonyl, halothioalkyl, alkoxyalkenyl, alkylsulphonamide, nitro,alkylsulphonyl, phenylsulphonyl or benzylsulphonyl; and b) a triazolederivative capable of inhibiting ergosterol biosynthesis in a (a)/(b)weight ratio of from 0.01 to 20, wherein the triazole derivative isazaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole,diniconazole, epoxiconazole, fenbuconazole, fluquinconazole,flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole,metconazole, myclobutanil, penconazole, propiconazole, prothioconazole,simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol,triticonazole, diclobutrazole, etaconazole, fluotrimazole, furconazole,furconazole-cis, triamiphos or triazbutil, and c) a further fungicidalcompound (c) different from a) and b) selected from the group consistingof trifloxystrobin, fluoxastrobin, picoxystrobin, pyraclostrobin,azoxystrobin, dimoxystrobin, and metominostrobin.
 2. A compositionaccording to claim 1, wherein p is
 2. 3. A composition according toclaim 1, wherein q is
 2. 4. A composition according to claim 1, whereinX, independently of the others, is halogen or haloalkyl.
 5. Acomposition according to claim 1, wherein X, independently of theothers, is a chloro atom or a trifluoromethyl group.
 6. A compositionaccording to claim 1, wherein Y, independently of the others, is halogenor haloalkyl.
 7. A composition according to claim 1, wherein Y,independently of the others, is a chloro atom or a trifluoromethylgroup.
 8. A composition according to claim 1, wherein the compound offormula (I) isN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide;N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-iodobenzamide;or N-{2-[3,5-dichloro-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide. 9.A composition according to claim 8, wherein the compound of formula (I)isN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide.10. A composition according to claim 1, wherein the fungicidal compound(c) is trifloxystrobin.
 11. A composition according to claim 1 furthercomprising an agriculturally acceptable support, carrier, filler and/orsurfactant.
 12. A method for preventively or curatively controllingphytopathogenic fungi of crops, wherein an effective and non-phytotoxicamount of a composition according to claim 1 is applied to the seed, theplant and/or to the fruit of the plant or to the soil in which the plantis growing or in which it is desired to grow.
 13. A compositionaccording to claim 1, wherein the triazole derivative isprothioconazole.
 14. A composition according to claim 1, wherein (a) thepyridylethylbenzamide derivative of formula (I) isN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide,(b) the triazole derivative capable of inhibiting the ergosterolbiosynthesis is prothioconazole, and (c) the further fungicidal compoundis trifloxystrobin.